1078129-19-7|ethyl 5-{[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate| Ambeed

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CAS No. :	1078129-19-7
Formula :	C₁₃H₁₈N₂O₄
M.W :	266.29
SMILES Code :	O=C(C1=NC=C(NC(OC(C)(C)C)=O)C=C1)OCC
MDL No. :	MFCD24471127

Yield	Reaction Conditions	Operation in experiment
78%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 6.5 h;	To a stirred solution of ethyl 5-(tert-butoxycarbonylarnino)picolinate (112; 8.9 g, 24.0 mmol) in ethyl ether (200 mL) was added LiAlH4 (1.80 g, 48 mmol) in ethyl ether (100 mL) over a period of 30 min at 0 ⁰C. The resulting reaction mixture was stirred at 0 ⁰C for 3 h and then carefully quenched by carefully adding water (1.0 mL) and 10percent NaOH solution (2.0 mL). The mixture was filtered; the filtrate was dried (Na₂SO₄) and concentrated under reduced pressure to afford tert-butyl 6-(hydroxymethyl)pyridin-3- ylcarbamate 113 (4.20 g, 78percent)
78%	Stage #1: With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3.5 h; Inert atmosphere Stage #2: With water; sodium hydroxide In diethyl ether at 0℃; Inert atmosphere	To a stirred solution of ethyl 5-(tert-butoxycarbonylamino)picolinate (18; 8.9 g, 24 mmol) in ethyl ether (200 mL) under nitrogen was added l ithium aluminum hydride (LAH) ( 1 .8 g, 48 mmol) in ethyl ether ( 100 mL) over a period of 30 min at 0 °C. The reaction mixture was stirred for 3 h, water ( 1 mL) and 1 0percent NaOH solution (2 mL) was added and the mixture was filtered and the filtrate was dried over a2SC>4 and concentrated under reduced pressure to give compound tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate (19; 4.2 g, 78percent). M S (ESI) calcd for C 1 1 H 16N2O3 (m/z) 224.26.
78%	With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3.5 h; Inert atmosphere	To a stirred solution of ethyl 5-(tert-butoxycarbonylamino)picolinate (8.9 g, 24 mmol) in ethyl ether (200 mL) under nitrogen was added LAH (1.8 g, 48 mmol) in ethyl ether (100 mL) over a period of 30 min at 0 °C. The reaction mixture was stirred for 3 h, water (1 mL) and 10percent NaOH solution (2 mL) was added and the mixture was filtered and the filtrate was dried over Na₂SO₄ and concentrated under reduced pressure to give compound tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate (4.2 g, 78percent). MS (ESI) calcd for C₁₁H₁₆N₂O₃ (m/z): 224.26

Yield	Reaction Conditions	Operation in experiment
78%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 6.5h;	To a stirred solution of ethyl 5-(tert-butoxycarbonylarnino)picolinate (112; 8.9 g, 24.0 mmol) in ethyl ether (200 mL) was added LiAlH4 (1.80 g, 48 mmol) in ethyl ether (100 mL) over a period of 30 min at 0 0C. The resulting reaction mixture was stirred at 0 0C for 3 h and then carefully quenched by carefully adding water (1.0 mL) and 10% NaOH solution (2.0 mL). The mixture was filtered; the filtrate was dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 6-(hydroxymethyl)pyridin-3- ylcarbamate 113 (4.20 g, 78%)
78%		To a stirred solution of ethyl 5-(tert-butoxycarbonylamino)picolinate (18; 8.9 g, 24 mmol) in ethyl ether (200 mL) under nitrogen was added l ithium aluminum hydride (LAH) ( 1 .8 g, 48 mmol) in ethyl ether ( 100 mL) over a period of 30 min at 0 C. The reaction mixture was stirred for 3 h, water ( 1 mL) and 1 0% NaOH solution (2 mL) was added and the mixture was filtered and the filtrate was dried over a2SC>4 and concentrated under reduced pressure to give compound tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate (19; 4.2 g, 78%). M S (ESI) calcd for C 1 1 H 16N2O3 (m/z) 224.26.
78%	With lithium aluminium tetrahydride; In diethyl ether; at 0℃; for 3.5h;Inert atmosphere;	To a stirred solution of ethyl 5-(tert-butoxycarbonylamino)picolinate (8.9 g, 24 mmol) in ethyl ether (200 mL) under nitrogen was added LAH (1.8 g, 48 mmol) in ethyl ether (100 mL) over a period of 30 min at 0 C. The reaction mixture was stirred for 3 h, water (1 mL) and 10% NaOH solution (2 mL) was added and the mixture was filtered and the filtrate was dried over Na2SO4 and concentrated under reduced pressure to give compound tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate (4.2 g, 78%). MS (ESI) calcd for C11H16N2O3 (m/z): 224.26

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Disposal
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CAS No.: 1078129-19-7

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CAS No.: 1078129-19-7

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[ 1078129-19-7 ] Synthesis Path-Upstream 1~1

[ 1078129-19-7 ] Synthesis Path-Downstream 1~2

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed